Enantioselective Synthesis of Pyrroloindolines by a Formal [3+2] Cycloaddition Reaction

被引：177
|
作者：
Repka, Lindsay M. [1 ]
Ni, Jane [1 ]
Reisman, Sarah E. [1 ]
机构：
[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 41期
关键词：
STREPTOMYCES SP SUC1; BRONSTED ACID; CHIRAL DIOLS; ASYMMETRIC ALLYLBORATION; LEWIS-ACID; ALKALOIDS; CONSTRUCTION; STRATEGY; EXAMPLE; ENONES;
D O I：
10.1021/ja107328g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(R)-BINOL center dot SnCl4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.
引用
收藏
页码：14418 / 14420
页数：3
相关论文
共 50 条
  • [21] Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3+2] Cycloaddition
    Cholewczynski, Anna E.
    Williams, Peyton C.
    Pierce, Joshua G.
    ORGANIC LETTERS, 2020, 22 (02) : 714 - 717
  • [22] Catalytic Intramolecular Formal [3+2] Cycloaddition for the Synthesis of Benzobicyclo[4.3.0] Compounds
    Han, Xun
    Ye, Long-Wu
    Sun, Xiu-Li
    Tang, Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3394 - 3397
  • [23] Enantioselective Dearomative [3+2] Cycloaddition Reactions of Benzothiazoles
    Wang, Dong-Chao
    Xie, Ming-Sheng
    Guo, Hai-Ming
    Qu, Gui-Rong
    Zhang, Meng-Cheng
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (45) : 14111 - 14115
  • [24] Synthesis of bicyclic proline analogs using a formal [3+2] intramolecular aziridine-allylsilane cycloaddition reaction
    Bergmeier, SC
    Fundy, SL
    Seth, PP
    TETRAHEDRON, 1999, 55 (26) : 8025 - 8038
  • [25] Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin-4-ones
    Shao, Pan-Lin
    Chen, Xiang-Yu
    Ye, Song
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8412 - 8416
  • [26] Novel [3+2] formal cycloaddition of allylsilanes to formal tetrahydrofurans.
    Angle, SR
    El-Said, NA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U182 - U182
  • [27] Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates
    Wang, Yang
    Wang, Qian
    Zhu, Jieping
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8084 - 8088
  • [28] Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines
    Kerr, Ryan W. F.
    Greenhalgh, Mark D.
    Slawin, Alexandra M. Z.
    Arnold, Polly L.
    Smith, Andrew D.
    TETRAHEDRON-ASYMMETRY, 2017, 28 (01) : 125 - 134
  • [29] Enantioselective [3+2] Formal Cycloaddition of 1-Styrylnaphthols with Quinones Catalyzed by a Chiral Phosphoric Acid
    Feng, Wang
    Yang, Hui
    Wang, Zhe
    Gou, Bo-Bo
    Chen, Jie
    Zhou, Ling
    ORGANIC LETTERS, 2018, 20 (10) : 2929 - 2933
  • [30] Enantioselective Synthesis of Spirooxindoles: Asymmetric [3+2] Cycloaddition of (3-Isothiocyanato)oxindoles with Azodicarboxylates
    Jiang, Yu
    Pei, Cheng-Kui
    Du, Dan
    Li, Xiao-Ge
    He, Ya-Nan
    Xu, Qin
    Shi, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (35) : 7895 - 7901
12345